Damon appears alongside George Clooney, Brad Pitt and Julia Roberts in Ocean's Eleven. The comic caper remake is a blockbuster hit, making more than $183 million during its five-month run in theaters. He also appears in the sequels, Ocean's Twelve in 2004 and Ocean's Thirteen in 2007.
Damon makes his debut as an action hero in The Bourne Identity, for which he makes $10 million playing an assassin with amnesia. In July 2004, The Bourne Supremacy is released, and Damon pockets a reported $15 million to return as Jason Bourne in the sequel, according to PEOPLE. The third installment, Bourne Ultimatum, is released in 2007.
Damon brings girlfriend Luciana Barroso, a part-time bartender in Miami Beach, home to meet his family and friends in Boston. A source tells PEOPLE that Damon and Barroso met in 2003 while he was filming Stuck on You. The following year, Damon, 34, proposes to Barroso, 29, and the pair weds on Dec. 9 in a top-secret ceremony at Manhattan's City Hall. Barroso's 7-year-old daughter (from a previous marriage), Alexia, and New York City Mayor Michael Bloomberg attend the ceremony.
May 2006 Damon takes a trip to Africa to embark on a six-day "listening and learning trip" with his brother Kyle through AIDS-ravaged Zambia. The actor, who is expecting a baby with his wife, tells PEOPLE, "The world I leave to my daughter is going to be affected by what I do, or what I don't do. The best way to honor and love her is to do what I can, here and now."
Damon and wife Luciana welcome daughter Isabella. "She definitely wanted a sister," the actor tells PEOPLE of his 7-year-old stepdaughter Alexia's wishes. In August 2008, the Damons welcome a third daughter, Gia Zavala. "It's a lot of pink, a lot of princesses and a lot of fun," he said of his "testosterone deficit" home life.
EW calls Damon's performance as a crooked cop in the star-studded crime drama The Departed "career-defining." By year's end, the actor delivers another acclaimed performance, opposite Angelina Jolie, in Robert DeNiro's The Good Shepherd.
After years of honorable mentions, Damon is finally named PEOPLE's Sexiest Man Alive in 2007. Friend and costar George Clooney – who has been named twice – has long advocated for Damon's win, telling PEOPLE in 2006, "If you've been around him, you know he's sexy. His eyes pop. They have a twinkle. He's got a good smile. He's quite the dancer. He does rock a Speedo in Ocean's 13." Damon says of the honor, "You've given an aging suburban dad the ego-boost of a lifetime."
In Clint Eastwood's Invictus, Damon plays a South African rugby player who helps President Nelson Mandela (Morgan Freeman) unite the country through the 1995 Rugby World Cup. "I felt completely fulfilled creatively," Damon tells PEOPLE of his role which earns him a Best Supporting Actor Oscar nomination. In 2010, Damon reunites with Eastwood for October's Hereafter.
Damon and wife Luciana welcome their fourth daughter, Stella Zavala Damon. "If I had a bucket list, I'd say raising my four girls to be strong, good women would be No. 1," the Hereafter star tells Parade of his hopes for his children, but adds, "Our lives are full and wonderful and we're done having kids."
Damon plays Texas Ranger LaBoeuf in the Coen Brothers' Oscar-nominated hit True Grit, opposite Jeff Bridges and newcomer Hailee Steinfeld. "This isn't the first time recently that I've delighted at how Damon has become one of Hollywood's most enjoyable, versatile actors," EW praises. "I'm happy every time I see him, and he's a great costar here, flavoring his LaBoeuf...with a piquant seasoning of Ranger vanity, bounty-hunting avarice, and Dudley Do-Right earnestness."
BIOGRAPHY (top to bottom): Bob Marshak/Warner Bros.; UNIVERSAL/KOBAL; ALLOCCA FERREIRA/STARTRAKS; J. TAYLOE EMERY; Jackson Lee/Splash News Online; Keith Bernstein/Warner Bros.; Alex J. Berliner/BEImages; Wilson Webb/Paramount Pictures